The education sector is a major generator, consumer, and depositary of educational content. Thanks to technological advances, today’s educators and learners have ubiquitous and on-demand access to information. Technology has made it possible for us to communicate and share information effortlessly from anywhere in the world. However, the availability of vast amounts of heterogeneous educational content will not be useful unless we search, retrieve and integrate it, creating interoperable educational environments. The current challenges to integrating educational content arise from its distribution over several repositories. This research proposes AIREH (architecture for intelligent retrieval of educational content from heterogeneous environments), for the retrieval of digital content through agent-based virtual organizations. This flexible architecture facilitates the search for and integration of heterogeneous content through an information retrieval model that involves both case-based reasoning and federated search. Moreover, AIREH is based on an adaptive organization model for distributed planning, thanks to which, it manages open systems flexibly, dynamically, and effectively. The conducted case study gives very promising results and demonstrates the advantages of using agent-based virtual organizations in the retrieval of labeled digital content. The proposed model is flexible, customizable, comprehensive and efficient.